The Chemistry of Metalated Arenesulfonyl Systems

Benzylic metalation is readily accomplished on appropriate diaryl sulfones, t-alkyl aryl sulfones and phenyl arenesulfonates and N-methylarenesulfonanilides. The resulting metalated sulfones undergo rearrangement to isomeric sulfinic acid salts, wherein an aryl or t-alkyl unit has moved from the sulfur atom to the benzylic carbanionoid center. The metalated arenesulfonates and sulfonanilides undergo coupling-condensation to form bibenzylic-type products. These rearrangements and coupling-condensations are interesting in their own right, and also offer considerable potential in synthetic work, inasmuch as they involve new carbon-carbon bond formations between a benzylic carbon and an aryl group or t-alkyl group or another benzylic carbon moiety, respectively.